MiMeDB: Showing metabocard for NAD (MMDBc0029513)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:25 UTC

Update Date

2024-04-30 19:36:44 UTC

Metabolite ID

MMDBc0029513

Metabolite Identification

Common Name

NAD

Description

NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305271900232D          

 44 48  0  0  1  0            999 V2000
    5.1419    0.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -0.7835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6127    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.4144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1306    1.9060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -0.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8536   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1720   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.6462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351    2.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3828   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -0.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -1.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0382   -0.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6974   -0.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4186   -1.6123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0851   -2.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5073   -0.0263    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.8820   -2.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8782    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2908    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8745    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    1.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    2.4410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4580    1.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  6  0  0  0
 33 36  1  1  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
 37 39  2  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 40 41  2  0  0  0  0
M  CHG  1  35   1
M  END


  Mrv1652305271900232D          

 44 48  0  0  1  0            999 V2000
    5.1419    0.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621    0.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347   -0.7835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6127    1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    0.4144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567   -0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6861   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1306    1.9060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6388    2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5937   -0.7684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8536   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1720   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.6462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6351    2.8817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -0.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3828   -2.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -1.4503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4934    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -0.5010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -1.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8551    0.4257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3563   -0.7572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0382   -0.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5711   -1.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6974   -0.8175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4186   -1.6123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0851   -2.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5073   -0.0263    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.8820   -2.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8782    0.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2908    0.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8745    1.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3021    1.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090    1.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1926    2.4410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4580    1.3448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  1  0  0  0
 32 35  1  6  0  0  0
 33 36  1  1  0  0  0
 35 37  1  0  0  0  0
 35 38  2  0  0  0  0
 37 39  2  0  0  0  0
 38 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 32 33  1  0  0  0  0
 40 41  2  0  0  0  0
M  CHG  1  35   1
M  END
> <DATABASE_ID>
MMDBc0029513

> <DATABASE_NAME>
MIME

> <SMILES>
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

> <INCHI_KEY>
BAWFJGJZGIEFAR-NNYOXOHSSA-O

> <FORMULA>
C21H28N7O14P2

> <MOLECULAR_WEIGHT>
664.433

> <EXACT_MASS>
664.116946663

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.833807292893255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-9.866487273821402

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1873599316560752

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8536300079335266

> <JCHEM_PKA_STRONGEST_BASIC>
4.009031974187107

> <JCHEM_POLAR_SURFACE_AREA>
318.2599999999999

> <JCHEM_REFRACTIVITY>
141.99689999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  N   UNK     0       9.598   1.097   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.143   1.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.211  -1.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.477   2.342   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.129   3.080   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.807   0.774   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       7.946  -0.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.747  -2.897   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.577   3.558   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.792   3.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.464   1.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.708  -1.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.193  -2.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.654  -4.135   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       5.457   3.073   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       6.786   5.379   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.267  -0.984   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.315  -4.135   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.036  -0.928   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       2.384  -0.921   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0       0.316  -0.928   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.384  -2.707   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.384   0.788   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      -1.596  -0.921   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      -3.242  -0.935   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.589  -2.630   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.596   0.795   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.838  -0.914   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.265  -1.413   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.538  -0.570   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.666  -2.974   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.768  -1.526   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.248  -3.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.759  -4.099   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0     -10.280  -0.049   0.000  0.00  0.00           N+1
HETATM   36  O   UNK     0      -9.113  -4.212   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -9.106   0.816   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -11.743   0.752   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.099   2.356   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -11.764   2.194   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.470   3.038   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.826   3.199   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -7.826   4.557   0.000  0.00  0.00           N+0
HETATM   44  O   UNK     0      -6.455   2.510   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   15                                                       
CONECT   12    7   17   13                                                  
CONECT   13    8   18   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10                                                            
CONECT   17   12   19                                                       
CONECT   18   13                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   24                                                       
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   21   25   26   27                                             
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   32                                                       
CONECT   31   29   33   34                                                  
CONECT   32   30   35   33                                                  
CONECT   33   31   36   32                                                  
CONECT   34   31                                                            
CONECT   35   32   37   38                                                  
CONECT   36   33                                                            
CONECT   37   35   39                                                       
CONECT   38   35   40                                                       
CONECT   39   37   41   42                                                  
CONECT   40   38   41                                                       
CONECT   41   39   40                                                       
CONECT   42   39   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

Synonyms

Value	Source
beta-NAD	ChEBI
Diphosphopyridine nucleotide	ChEBI
DPN	ChEBI
NAD+	ChEBI
Nadide	ChEBI
Nicotinamide adenine dinucleotide	ChEBI
beta-NAD+	Kegg
b-NAD	Generator
Β-nad	Generator
b-NAD+	Generator
Β-nad+	Generator
3-Carbamoyl-1-beta-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt	HMDB
3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt	HMDB
3-Carbamoyl-1-D-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate	HMDB
3-Carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate	HMDB
Adenine-nicotinamide dinucleotide	HMDB
beta-Diphosphopyridine nucleotide	HMDB
beta-Nicotinamide adenine dinucleotide	HMDB
beta-Nicotinamide adenine dinucleotide trihydrate	HMDB
CO-I	HMDB
Codehydrase I	HMDB
Codehydrogenase I	HMDB
Coenzyme I	HMDB
Cozymase	HMDB
Cozymase I	HMDB
Diphosphopyridine nucleotide oxidized	HMDB
Endopride	HMDB
NAD trihydrate	HMDB
NAD-oxidized	HMDB
Nicotinamide adenine dinucleotide oxidized	HMDB
Nicotinamide dinucleotide	HMDB
Nicotineamide adenine dinucleotide	HMDB
Oxidized diphosphopyridine nucleotide	HMDB
Pyridine nucleotide diphosphate	HMDB
[(3S,2R,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,2R,4R,5R)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate	HMDB
[Adenylate-32-p]-NAD	HMDB
Dihydronicotinamide adenine dinucleotide	HMDB
NADH	HMDB
Nucleotide, diphosphopyridine	HMDB
Adenine dinucleotide, dihydronicotinamide	HMDB
Dinucleotide, dihydronicotinamide adenine	HMDB
Dinucleotide, nicotinamide-adenine	HMDB
Nicotinamide-adenine dinucleotide	HMDB

Molecular Formula

C₂₁H₂₈N₇O₁₄P₂

Average Mass

664.433

Monoisotopic Mass

664.116946663

IUPAC Name

1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

Traditional Name

1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium

CAS Registry Number

53-84-9

SMILES

NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI Key

BAWFJGJZGIEFAR-NNYOXOHSSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

(5'->5')-dinucleotide
Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Nicotinamide-nucleotide
Pyridine nucleotide
Pentose-5-phosphate
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Purine
Imidazopyrimidine
Nicotinamide
Monoalkyl phosphate
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Imidolactam
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Pyridinium
Pyridine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Carboximidic acid derivative
Carboximidic acid
Organoheterocyclic compound
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

NAD(P)(+) (CHEBI:15846 )
NAD (CHEBI:15846 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-9.9	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	1.85	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	318.26 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142 m³·mol⁻¹	ChemAxon
Polarizability	55.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-4213904000-b8a6dbd0370f9d5a56be	2017-09-01	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-006x-0011297400-efee4fe3a4cf024c960a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0028900000-8ec9bcaf25513495b979	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0011953000-577487fb6aff29c77330	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0000009000-e1d0afb4e7926a0f845e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0001092010-1dcbca7a5ffe61f23e50	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0028900000-764e3ecea72fe178a87e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0018900000-3b774fba9b96129baa6c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0000090000-d4236efb9eec36017416	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0000029000-870aa620464a4fedbe8d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-002r-0930610000-ccd233f26036136ba3e8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-0900000000-ec77ba41ae7dbcfd08a2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00dl-0219003700-2f52e3c5db41066a112c	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0uk9-0301009000-a3d0c464e56f6e320c80	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00dl-0000090000-c18a7719161c63a71938	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0000009000-1dde5b221786fe375304	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0911001000-bd16ca8021ab63e9e290	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0900000000-662adda5a00fce5c5017	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-0900000000-a2724dbab2ca6eb7e8da	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00dl-0400090000-19bb49ef6fe960f224d2	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000009000-0b37b39334338eb59ba4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1100109000-7b9f7c9d8d96bfbfe848	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rt-9300000000-34fd3df485912f4e75a4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000009000-b658a57d72fd6ec693f9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0000009000-841f81c695ad2c0ec387	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-7920202000-c7820b4eaef53b5cdf66	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Endoplasmic reticulum
Extracellular
Mitochondria
Nucleus
Peroxisome

Biospecimen Locations

Adrenal Gland
Blood
Brain
Cellular Cytoplasm
Epidermis
Feces
Fibroblasts
Liver
Placenta
Platelet
Prostate
Skeletal Muscle

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000020	1-Piperideine-2-carboxylic acid	L-Pipecolic acid	Not Available	VMH; KEGG	10485319 10772957
MMDBr0000041	2-Hydroxybutyric acid	2-Ketobutyric acid	lactate dehydrogenase A	VMH; KEGG	10108 21765
MMDBr0000045	Oxoadipic acid	Glutaryl-CoA	dihydrolipoamide dehydrogenase	VMH; KEGG	30371894
MMDBr0000047	3,4-Dihydroxymandelaldehyde	3,4-Dihydroxyphenylglycol	Not Available	VMH; KEGG	3466164
MMDBr0000051	3,4-Dihydroxyphenylacetaldehyde	3,4-Dihydroxybenzeneacetic acid	aldehyde dehydrogenase 1 family, member A3	VMH	11306106 2071588
MMDBr0000053	3,4-Dihydroxymandelaldehyde	3,4-Dihydroxymandelic acid	aldehyde dehydrogenase 1 family, member A3	VMH	10424772 12616643
MMDBr0000055	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available	VMH; KEGG	11583838 12232327
MMDBr0000060	3-Decaprenyl-4-Hydroxybenzoate	3,4-dihydroxy-5-all-trans-decaprenylbenzoate	Not Available	VMH	11051212
MMDBr0000069	Hydroxypropionic acid	Malonic semialdehyde	Not Available	VMH	4507604
MMDBr0000072	Homovanillin	Homovanillic acid	aldehyde dehydrogenase 1 family, member A3	VMH	6422947 9732974
MMDBr0000076	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	aldehyde dehydrogenase 1 family, member A3	VMH	30371894
MMDBr0000091	4-Coumaroyl-CoA	4-hydroxybenzoyl-CoA	Not Available	VMH; KEGG	11583838 12232327
MMDBr0000094	L-4-hydroxyglutamic semialdehyde	L-Glutamyl-tRNA(Glu)	aldehyde dehydrogenase 4 family, member A1	VMH; KEGG	15849464
MMDBr0000117	5-Hydroxyindoleacetaldehyde	5-Hydroxyindoleacetic acid	aldehyde dehydrogenase 1 family, member B1	VMH	11306106
MMDBr0000142	Allysine	Aminoadipic acid	Not Available	VMH; KEGG	15865210
MMDBr0000145	L-Arabitol	L-Threo-2-pentulose	Not Available	VMH; KEGG	12359133 13922173 15234337
MMDBr0000254	Oxoglutaric acid	Succinyl-CoA	dihydrolipoamide dehydrogenase	VMH; KEGG	1542694
MMDBr0000259	7a-Hydroxy-5b-cholestan-3-one	3a,7a-Dihydroxy-5b-cholestane	aldo-keto reductase family 1, member C4	VMH	30371894
MMDBr0000275	Propylene glycol	D-Lactaldehyde	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH; KEGG	15987839 2296157
MMDBr0000276	(S)-Propane-1,2-diol	Lactaldehyde	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH	15987839 2296157
MMDBr0000277	D-Lactaldehyde	BPG	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH	15987839 2296157
MMDBr0000278	Lactaldehyde	BPG	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH; KEGG	15987839 2296157
MMDBr0000279	Ethanol	Acetaldehyde	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH	11762128 12592711
MMDBr0000281	Indoleacetaldehyde	Indoleacetic acid	aldehyde dehydrogenase 1 family, member A1	VMH; KEGG	18983992 18983993 9884322
MMDBr0000282	Indoleacetaldehyde	Indoleacetic acid	aldehyde dehydrogenase 1 family, member B1	VMH; KEGG	18983992 18983993 6377948
MMDBr0000283	Pristanal	Pristanic acid	aldehyde dehydrogenase 3 family, member A2	VMH	11591435 8528251
MMDBr0000284	Acetaldehyde	Acetic acid	aldehyde dehydrogenase 1 family, member B1	VMH; KEGG	18983992 18983993 19382904 19382905
MMDBr0000374	3-Aminopropionaldehyde	beta-Alanine	Not Available	VMH	12586697
MMDBr0000375	3-Aminopropionaldehyde	beta-Alanine	aldehyde dehydrogenase 1 family, member B1	VMH	30371894
MMDBr0000379	(R)-3-Hydroxybutyric acid	Acetoacetic acid	3-hydroxybutyrate dehydrogenase, type 1	VMH; KEGG	1639787 8679568
MMDBr0000382	Betaine aldehyde	Betaine	Not Available	VMH; KEGG	15321791
MMDBr0000437	4beta-methylzymosterol-4alpha-carboxylic acid	3-Keto-4-methylzymosterol	NAD(P) dependent steroid dehydrogenase-like	VMH	12829805
MMDBr0000441	3-Keto-4-methylzymosterol	zymosterol intermediate 2	methylsterol monooxygenase 1	VMH	30371894
MMDBr0000449	Aquacobalamin	Cob(II)alamin	Not Available	VMH	14633777
MMDBr0000646	Palmityl-CoA	Palmitoleyl-CoA	stearoyl-CoA desaturase (delta-9-desaturase)	VMH	14967823
MMDBr0000647	Alpha-Linolenoyl-CoA	Stearidonoyl CoA	fatty acid desaturase 2	VMH	30371894
MMDBr0000648	Stearoyl-CoA	oleoyl-CoA	stearoyl-CoA desaturase (delta-9-desaturase)	VMH	14967823
MMDBr0000649	Stearoyl-CoA	11-Octadecenoyl Coenzyme A	stearoyl-CoA desaturase (delta-9-desaturase)	VMH	14967823
MMDBr0000650	Stearoyl-CoA	Trans-Octadec-2-enoyl-CoA	stearoyl-CoA desaturase (delta-9-desaturase)	VMH	14967823
MMDBr0000651	Linoleoyl-CoA	Gamma-linolenoyl-CoA	fatty acid desaturase 1	VMH	30371894
MMDBr0000652	8Z,11Z,14Z-eicosatrienoyl-CoA	Arachidonyl-CoA	fatty acid desaturase 1	VMH	30371894
MMDBr0000653	Eicosatetranoyl coenzyme A	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	fatty acid desaturase 1	VMH	30371894
MMDBr0000654	Adrenyl coenzyme A	Docosa-4,7,10,13,16-pentaenoyl CoA	Not Available	VMH	30371894
MMDBr0000655	Clupanodonyl CoA	Cervonyl Coenzyme A	Not Available	VMH	30371894
MMDBr0000656	(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoyl Coenzyme A	Tetracosahexaenoyl CoA	fatty acid desaturase 2	VMH	30371894
MMDBr0001144	Formaldehyde	S-Formylglutathione	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	4436331 8460164
MMDBr0001147	4,8 Dimethylnonanoyl Coenzyme A	2,6 Dimethylheptanoyl Coenzyme A	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	9819701
MMDBr0001148	Tetradecanoyl-CoA	Acetyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344
MMDBr0001149	Pentadecanoyl Coenzyme A	Propionyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344
MMDBr0001150	Palmityl-CoA	Acetyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001151	Palmityl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001152	Palmityl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001153	(2E)-Hexadecenoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001154	Palmitoleyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001155	Heptadecanoyl Coenzyme A	Propionyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344
MMDBr0001156	Stearoyl-CoA	Palmityl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001157	Stearoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001158	Trans-Octadec-2-enoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001159	11-Octadecenoyl Coenzyme A	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001160	oleoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001161	Linoleoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001162	Alpha-Linolenoyl-CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001163	Gamma-linolenoyl-CoA	Hydrogen peroxide	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001164	Gamma-linolenoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001165	Stearidonoyl CoA	Octanoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001166	Stearidonoyl CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001167	Eicosanoyl-CoA	Stearoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001168	Eicosanoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001169	8Z,11Z,14Z-eicosatrienoyl-CoA	Gamma-linolenoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001170	Arachidonyl-CoA	Acetyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001171	Eicosatetranoyl coenzyme A	Stearidonoyl CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001172	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Stearidonoyl CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001173	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	Stearidonoyl CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001174	Adrenyl coenzyme A	Arachidonyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001175	Adrenyl coenzyme A	Arachidonyl-CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001176	Docosa-4,7,10,13,16-pentaenoyl CoA	Gamma-linolenoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001177	Docosa-4,7,10,13,16-pentaenoyl CoA	Gamma-linolenoyl-CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001178	Docosa-4,7,10,13,16-pentaenoyl CoA	Hydrogen peroxide	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	30371894
MMDBr0001179	Docosa-4,7,10,13,16-pentaenoyl CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001180	Cervonyl Coenzyme A	Acetyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001181	Cervonyl Coenzyme A	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001182	Cervonyl Coenzyme A	(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl-CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001183	Tetracosanoyl-CoA	Eicosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001184	Nervonyl CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001185	Tetracosatetraenoyl CoA	Adrenyl coenzyme A	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001186	(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoyl Coenzyme A	Clupanodonyl CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001187	Tetracosapentaenoyl coenzyme A, n-6	Docosa-4,7,10,13,16-pentaenoyl CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001188	Tetracosahexaenoyl CoA	Cervonyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001189	hexacosanoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0001190	Octanoyl-CoA	Acetyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	2565344 3035565
MMDBr0001211	Formic acid	Carbon dioxide	Not Available	VMH; KEGG	30371894
MMDBr0001258	Glucose 6-phosphate	6-Phosphonoglucono-D-lactone	hexose-6-phosphate dehydrogenase (glucose 1-dehydrogenase)	VMH	10349511 12831846 2156506
MMDBr0001271	Glycolaldehyde	Glycolic acid	aldehyde dehydrogenase 18 family, member A1	VMH; KEGG	11434452 9038835
MMDBr0001274	Dihydrolipoamide	Lipoamide	aminomethyltransferase	VMH; KEGG	15355973
MMDBr0001309	D-Glucurono-6,3-lactone	Glucaric acid	Not Available	VMH	3779687
MMDBr0001310	D-Glucurono-6,3-lactone	Glucaric acid	aldehyde dehydrogenase 1 family, member B1	VMH	3779687
MMDBr0001337	L-Glutamic acid	Oxoglutaric acid	glutamate dehydrogenase 1	VMH	12324473 3368458
MMDBr0001396	L-Gulonate	3-Dehydro-L-gulonate	Not Available	VMH; KEGG	30371894
MMDBr0001413	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	hydroxyacyl-CoA dehydrogenase	VMH; KEGG	30371894
MMDBr0001414	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH; KEGG	30371894
MMDBr0001415	2-Methyl-3-hydroxybutyryl-CoA	2-Methylacetoacetyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH; KEGG	30371894
MMDBr0001436	(S)-3-Hydroxyisobutyric acid	2-Methyl-3-oxopropanoic acid	3-hydroxyisobutyrate dehydrogenase	VMH; KEGG	30371894
MMDBr0001463	Hydroxypyruvic acid	L-Glyceric acid	lactate dehydrogenase A	VMH	14635115 5635456
MMDBr0001468	Cortisone	Cortisol	hydroxysteroid (11-beta) dehydrogenase 2	VMH	11673786 15466942 7859916
MMDBr0001472	Estrone	Estradiol	hydroxysteroid (17-beta) dehydrogenase 2	VMH; KEGG	30371894
MMDBr0001474	Androstanedione	Androsterone	aldo-keto reductase family 1, member C4	VMH	14643063 7650035
MMDBr0001476	Pregnenolone	Progesterone	Not Available	VMH	16023337
MMDBr0001477	Pregnenolone	Progesterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	VMH	16023337
MMDBr0001478	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Not Available	VMH	12205101
MMDBr0001479	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	VMH	12205101
MMDBr0001480	16a-Hydroxydehydroisoandrosterone	Androstanedione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	VMH	11384872 14643063
MMDBr0001492	Isocitric acid	Oxoglutaric acid	isocitrate dehydrogenase 3 (NAD+) alpha	VMH; KEGG	30371894
MMDBr0001506	Imidazole-4-acetaldehyde	Imidazoleacetic acid	aldehyde dehydrogenase 1 family, member B1	VMH	2071588
MMDBr0001538	Glutathione	S-Lactoylglutathione	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH; KEGG	30371894
MMDBr0001539	BPG	D-Lactaldehyde	aldo-keto reductase family 7, member A2 (aflatoxin aldehyde reductase)	VMH	12071861 9823300
MMDBr0001541	D-Lactaldehyde	D-Lactic acid	Not Available	VMH; KEGG	30371894
MMDBr0001542	D-Lactaldehyde	D-Lactic acid	aldehyde dehydrogenase 18 family, member A1	VMH	15987839 2296157 6487654
MMDBr0001543	Lactaldehyde	L-Lactic acid	aldehyde dehydrogenase 18 family, member A1	VMH	15987839 2296157 6487654
MMDBr0001607	Methylimidazole acetaldehyde	Methylimidazoleacetic acid	aldehyde dehydrogenase 1 family, member A3	VMH	10344773
MMDBr0001626	L-Cysteine	3-Mercaptolactate-cysteine disulfide	Not Available	VMH	6945862
MMDBr0001627	3-Mercaptolactic acid	3-Mercaptopyruvic acid	Not Available	VMH	7054184
MMDBr0001629	(S)-malate(2-)	Oxalacetic acid	malate dehydrogenase 1, NAD (soluble)	VMH; KEGG	30371894
MMDBr0001686	2-Methyl-3-oxopropanoic acid	Propionyl-CoA	aldehyde dehydrogenase 6 family, member A1	VMH; KEGG	30371894
MMDBr0001688	2-Methyl-3-oxopropanoic acid	R-Methylmalonyl-CoA	Not Available	VMH	1527093
MMDBr0001691	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolase	VMH; KEGG	30371894
MMDBr0001694	4-acetamidobutanal	4-Acetamidobutanoic acid	aldehyde dehydrogenase 1 family, member A1	VMH; KEGG	30371894
MMDBr0001695	4-acetamidobutanal	4-Acetamidobutanoic acid	aldehyde dehydrogenase 1 family, member B1	VMH	30371894
MMDBr0001699	Ubiquinone-1	Ubiquinol-10	Not Available	VMH	19185523 19185524 7180843
MMDBr0001823	Ketoleucine	Isovaleryl-CoA	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH; KEGG	30371894
MMDBr0001824	alpha-Ketoisovaleric acid	Isobutyryl-CoA	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH; KEGG	30371894
MMDBr0001825	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH	1429740 2914958
MMDBr0001882	7a-Hydroxy-cholestene-3-one	7a,12a-Dihydroxy-cholestene-3-one	cytochrome P450, family 8, subfamily B, polypeptide 1	VMH	30371894
MMDBr0001884	L-D-1-Pyrroline-5-carboxylic acid	L-Glutamic acid	aldehyde dehydrogenase 4 family, member A1	VMH; KEGG	30371894
MMDBr0001886	L-D-1-Pyrroline-5-carboxylic acid	L-Proline	pyrroline-5-carboxylate reductase 1	VMH; KEGG	30371894
MMDBr0001915	Pristanoyl Coenzyme A	4,8 Dimethylnonanoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	11591435 12814641 15599942 1679347 7487879 8188243
MMDBr0001919	3-Phospho-D-glycerate	Phosphohydroxypyruvic acid	phosphoglycerate dehydrogenase	VMH; KEGG	30371894
MMDBr0001928	Pyrroline hydroxycarboxylic acid	L-Glutamyl-tRNA(Glu)	aldehyde dehydrogenase 4 family, member A1	VMH; KEGG	30371894
MMDBr0001976	D-Lactaldehyde	Propylene glycol	aldo-keto reductase family 7, member A2 (aflatoxin aldehyde reductase)	VMH	12071861 9823300
MMDBr0001997	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	proline dehydrogenase (oxidase) 1	VMH	10192398
MMDBr0002043	Perillyl aldehyde	Perillic acid	aldehyde dehydrogenase 1 family, member A1	VMH	30371894
MMDBr0002044	Perillyl aldehyde	Perillic acid	aldehyde dehydrogenase 1 family, member B1	VMH	30371894
MMDBr0002049	Retinal	all-trans-Retinoic acid	Not Available	VMH; KEGG	30371894
MMDBr0002051	13-cis-Retinal	13-cis-Retinoic acid	Not Available	VMH	11606944
MMDBr0002062	Vitamin A	Retinal	Not Available	VMH; KEGG	30371894
MMDBr0002064	Vitamin A	Retinal	retinol dehydrogenase 5 (11-cis/9-cis)	VMH	12226107 1503811 7836368 9115228
MMDBr0002066	Vitamin A	Retinal	retinol dehydrogenase 5 (11-cis/9-cis)	VMH	12226107 1503811 7836368
MMDBr0002068	13-cis Retinol	13-cis-Retinal	retinol dehydrogenase 5 (11-cis/9-cis)	VMH	9115228
MMDBr0002097	Sorbitol	D-Fructose	Not Available	VMH; KEGG	30371894
MMDBr0002134	(S)-3-Sulfonatolactate	3-Sulfopyruvic acid	malate dehydrogenase 1, NAD (soluble)	VMH; KEGG	30371894
MMDBr0002135	(S)-3-Sulfonatolactate	3-Sulfopyruvic acid	malate dehydrogenase 2, NAD (mitochondrial)	VMH	15758220 3346220
MMDBr0002255	4-Trimethylammoniobutanal	4-Trimethylammoniobutanoic acid	aldehyde dehydrogenase 9 family, member A1	VMH	10702312 8645224 8786138
MMDBr0002268	Ubiquinone-1	Ubiquinol-10	thioredoxin reductase 1	VMH	12435734 8577704 8999974
MMDBr0002312	Uridine diphosphate glucose	UDP-Glucuronic acid	UDP-glucose 6-dehydrogenase	VMH; KEGG	30371894
MMDBr0002390	Xanthine	Uric acid	xanthine dehydrogenase	VMH; KEGG	30371894
MMDBr0002407	D-Xylitol	D-Xylulose	Not Available	VMH	6821187
MMDBr0002437	Glutathione	Oxidized glutathione	glutathione reductase	VMH	10781871 12821209 237878 31912 4380255 8981046 9621574
MMDBr0002438	Glutathione	Oxidized glutathione	glutathione reductase	VMH	10781871 12821209 237878 31912 4380255 8981046 9621574
MMDBr0002449	L-Glutamic-gamma-semialdehyde	L-Glutamic acid	aldehyde dehydrogenase 4 family, member A1	VMH; KEGG	30371894
MMDBr0002477	Succinic acid semialdehyde	Succinic acid	aldehyde dehydrogenase 5 family, member A1	VMH	3190233 656447 7616245 7814412
MMDBr0002484	Glycerol 3-phosphate	Dihydroxyacetone phosphate	glycerol-3-phosphate dehydrogenase 1 (soluble)	VMH; KEGG	30371894
MMDBr0002489	Dihydrofolic acid	Tetrahydrofolic acid	dihydrofolate reductase	VMH	15153070 1631094 6882460
MMDBr0002491	Dihydrouracil	Uracil	Not Available	VMH	1260500
MMDBr0002497	Cytidine 5'-monophosphate-N-acetylneuraminic acid	CMP-N-glycoloylneuraminate	Not Available	VMH	11211935 2249689 8112313
MMDBr0002512	Thymine	Dihydrothymine	Not Available	VMH; KEGG	30371894
MMDBr0002513	Thymine	Dihydrothymine	Not Available	VMH; KEGG	30371894
MMDBr0002523	Hydroxypropionic acid	Malonic semialdehyde	Not Available	VMH; KEGG	30371894
MMDBr0002526	Hypotaurine	Taurine	Not Available	VMH	13979247 16680556 7295801
MMDBr0002535	D-Glyceraldehyde	Glyceric acid	aldehyde dehydrogenase 1 family, member B1	VMH; KEGG	30371894
MMDBr0002536	Hypoxanthine	Xanthine	xanthine dehydrogenase	VMH	2713424 8248161
MMDBr0002539	N-Acetylneuraminic acid	N-Glycolylneuraminic acid	Not Available	VMH	11522391 12192086
MMDBr0002549	Isocitric acid	Oxalosuccinic acid	isocitrate dehydrogenase 1 (NADP+), soluble	VMH	10521434 16489927 18484410 9866202
MMDBr0002575	Xanthine	Uric acid	Not Available	VMH	11246119 12632927
MMDBr0002578	Dihydrofolic acid	Folic acid	dihydrofolate reductase	VMH; KEGG	30371894
MMDBr0002583	Saccharopine	L-Glutamic acid	aminoadipate-semialdehyde synthase	VMH; KEGG	30371894
MMDBr0002589	Phenylacetaldehyde	Phenylacetic acid	Not Available	VMH	15230339
MMDBr0002590	Phenylacetaldehyde	Phenylacetic acid	aldehyde dehydrogenase 1 family, member A3	VMH; KEGG	30371894
MMDBr0002593	4-Aminobutyraldehyde	gamma-Aminobutyric acid	aldehyde dehydrogenase 1 family, member B1	VMH	2925663 8155713 8269919 8786138 9417993
MMDBr0002594	Betaine aldehyde	Betaine	aldehyde dehydrogenase 7 family, member A1	VMH	10505788 7646513
MMDBr0002599	Gentisate aldehyde	Gentisic acid	Not Available	VMH; KEGG	30371894
MMDBr0002614	Allysine	Aminoadipic acid	Not Available	VMH	2160277
MMDBr0002623	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0002624	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	pyrroline-5-carboxylate reductase 1	VMH	12514185 3768405 6250440 675382
MMDBr0002628	3Alpha,7Alpha,12Alpha-Trihydroxy-5Beta-Cholestan-26-Al	3a,7a,12a-Trihydroxy-5b-cholestanoic acid	Not Available	VMH	1591235 5723340 5914340
MMDBr0002629	3a,7a-Dihydroxy-5b-cholest-24-enoyl-CoA	3Alpha,7Alpha,12Alpha-Trihydroxy-5Beta-Cholestan-26-Al	Not Available	VMH	1591235 6338006
MMDBr0002640	2-Methyl-3-oxopropanoic acid	Methylmalonic acid	aldehyde dehydrogenase 1 family, member B1	VMH	10947204 10989432 1527093 16683190 8120000 8155713 8634152 9787093
MMDBr0002641	2-Methyl-3-oxopropanoic acid	Methylmalonic acid	aldehyde dehydrogenase 1 family, member B1	VMH	10947204 10989432 1527093 16683190 8120000 8155713 8634152 9787093
MMDBr0002643	2-Aminomuconic acid semialdehyde	2-Aminomuconic acid	Not Available	VMH	30371894
MMDBr0002665	3a,7a-Dihydroxy-5b-cholestan-26-al	3a,7a-Dihydroxycoprostanic acid	aldehyde dehydrogenase 1 family, member B1	VMH	11182138 8155713 9538213
MMDBr0002671	(S)-3-Hydroxyhexadecanoyl-CoA	3-Oxohexadecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002672	(S)-3-Hydroxyhexadecanoyl-CoA	3-Oxohexadecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002675	(S)-3-Hydroxytetradecanoyl-CoA	3-Oxotetradecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002676	(S)-3-Hydroxytetradecanoyl-CoA	3-Oxotetradecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002679	(S)-3-Hydroxydodecanoyl-CoA	3-Oxododecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002680	(S)-3-Hydroxydodecanoyl-CoA	3-Oxododecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002682	(S)-Hydroxydecanoyl-CoA	3-Oxodecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002683	(S)-Hydroxydecanoyl-CoA	3-Oxodecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002686	(S)-Hydroxyoctanoyl-CoA	3-Oxooctanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002689	(S)-Hydroxyhexanoyl-CoA	3-Oxohexanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10231530 10329704 1550553 1651711 7150615 8188243 8687463 9553139
MMDBr0002693	3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane	3a,7a-Dihydroxy-5b-cholestan-26-al	Not Available	VMH	5487878 6338006 6379302
MMDBr0002697	3,4-Dihydroxymandelaldehyde	3,4-Dihydroxymandelic acid	aldehyde dehydrogenase 1 family, member A3	VMH	10424772 11958479 3466164
MMDBr0002699	Homovanillin	Homovanillic acid	aldehyde dehydrogenase 1 family, member A3	VMH	17379813 18621017
MMDBr0002701	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	aldehyde dehydrogenase 1 family, member A3	VMH	17379813 18621017
MMDBr0002703	5-Hydroxyindoleacetaldehyde	5-Hydroxyindoleacetic acid	aldehyde dehydrogenase 1 family, member B1	VMH	8155713 8605195
MMDBr0002712	GDP-4-Dehydro-6-deoxy-D-mannose	GDP-L-Fucose	tissue specific transplantation antigen P35B	VMH	10410995 2428310 9603974
MMDBr0002714	D-Xylitol	L-Threo-2-pentulose	Not Available	VMH; KEGG	30371894
MMDBr0002721	D-Ribose	Ribitol	Not Available	VMH	15234337
MMDBr0002865	2-Ketobutyric acid	Propionyl-CoA	branched chain keto acid dehydrogenase E1, alpha polypeptide	VMH	2649080 283398 3718468 9381974
MMDBr0002935	S-(Hydroxymethyl)glutathione	S-Formylglutathione	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	18288723
MMDBr0002977	(S)-3-Hydroxyoleyleoyl Coenzyme A	3-Oxooleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0003838	(3S)-3-Hydroxylinoleoyl-CoA	3-Oxolinoleoyl Coenzyme A	Not Available	VMH	7846063
MMDBr0003839	(3S)-3-Hydroxylinoleoyl-CoA	3-Oxolinoleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7846063
MMDBr0003840	(3S)-3-Hydroxylinoleoyl-CoA	3-Oxolinoleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7846063
MMDBr0003976	23S,25-dihydroxyvitamin D3	23S,25,26-Trihydroxyvitamin D3	Not Available	VMH	11012668
MMDBr0003977	Secalciferol	23S,25,26-Trihydroxyvitamin D3	cytochrome P450, family 24, subfamily A, polypeptide 1	VMH	11012668
MMDBr0003982	Mannitol	L-Sorbose	Not Available	VMH	6870831
MMDBr0003983	Sorbitol	D-Glucose	Not Available	VMH	9537432
MMDBr0004001	(3S)-3-Hydroxy-cis,cis-palmito-7,10-dienoyl-CoA	3-Oxo-Cis,Cis-7,10-Hexadecadienoyl Coenzyme A	Not Available	VMH	10407780 7775433
MMDBr0004002	(3S)-3-Hydroxy-cis,cis-palmito-7,10-dienoyl-CoA	3-Oxo-Cis,Cis-7,10-Hexadecadienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 7775433
MMDBr0004003	(3S)-3-Hydroxy-cis,cis-palmito-7,10-dienoyl-CoA	3-Oxo-Cis,Cis-7,10-Hexadecadienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 7775433
MMDBr0004004	3(S)-Hydroxy-5Z,8Z-Tetradecadienoyl Coenzyme A	3-Oxo-Cis,Cis-5,8-Tetradecadienoyl Coenzyme A	Not Available	VMH	11451959
MMDBr0004005	3(S)-Hydroxy-5Z,8Z-Tetradecadienoyl Coenzyme A	3-Oxo-Cis,Cis-5,8-Tetradecadienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11451959
MMDBr0004006	3(S)-Hydroxy-5Z,8Z-Tetradecadienoyl Coenzyme A	3-Oxo-Cis,Cis-5,8-Tetradecadienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11451959
MMDBr0004007	(3S)-3-Hydroxydodec-cis-6-enoyl-CoA	3-Oxolaur-6-Cis-Enoyl Coenzyme A	Not Available	VMH	11451959
MMDBr0004008	(3S)-3-Hydroxydodec-cis-6-enoyl-CoA	3-Oxolaur-6-Cis-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11451959
MMDBr0004009	(3S)-3-Hydroxydodec-cis-6-enoyl-CoA	3-Oxolaur-6-Cis-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	0
MMDBr0004050	7a-Hydroxycholesterol	7a-Hydroxy-cholestene-3-one	Not Available	VMH	10599696 11067870 11454857 1401999
MMDBr0004051	7a-Hydroxycholesterol	7a-Hydroxy-cholestene-3-one	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	10599696 11067870 11454857 1401999
MMDBr0004052	5Beta-Cholestane-3Alpha,7Alpha,27-Triol	3a,7a-Dihydroxy-5b-cholestan-26-al	Not Available	VMH	9660774
MMDBr0004053	3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane	3a,7a-Dihydroxy-5b-cholestan-26-al	cytochrome P450, family 27, subfamily A, polypeptide 1	VMH	9660774
MMDBr0004110	Spermidine	Dehydrospermidine	Not Available	VMH; KEGG	30371894
MMDBr0004113	13-cis-Retinal	13-cis-Retinoic acid	Not Available	VMH	10559215 11007799
MMDBr0004192	Vitamin A2	All-Trans-3,4-Didehydroretinoate	Not Available	VMH	9647871
MMDBr0004193	5a-Pregnane-3,20-dione	Allopregnanolone	Not Available	VMH	12416991
MMDBr0004194	Allopregnanolone	Tetrahydrodeoxycorticosterone	Not Available	VMH	12376740
MMDBr0004195	Allopregnanolone	Tetrahydrodeoxycorticosterone	cytochrome P450, family 21, subfamily A, polypeptide 2	VMH	12376740
MMDBr0004198	7-Dehydrocholesterol	27Alpha-Hydroxy-7-Dehydrocholesterol	Not Available	VMH	11254748 12581873
MMDBr0004199	8-Dehydrocholesterol	27Alpha-Hydroxy-8-Dehydrocholesterol	Not Available	VMH	11254748 12581873
MMDBr0004200	8-Dehydrocholesterol	27Alpha-Hydroxy-8-Dehydrocholesterol	cytochrome P450, family 27, subfamily A, polypeptide 1	VMH	11254748 12581873
MMDBr0004219	Leucinic acid	Ketoleucine	Not Available	VMH	6434570 6688766
MMDBr0004233	Spermidine Monoaldehyde 1	Putreanine	Not Available	VMH	10047787 7040832
MMDBr0004234	Spermidine Monoaldehyde 2	Isoputreanine	Not Available	VMH	10047787 7040832
MMDBr0004235	Spermine Monoaldehyde	Spermic Acid 1	Not Available	VMH	10047787 7040832
MMDBr0004265	3-Hydroxykynurenine-O-Beta-D-Glucoside	4-(2-Amino-3-Hydroxyphenyl)-4-Oxobutanoic Acid O-Glucoside	Not Available	VMH	10409626
MMDBr0004314	27-Deoxy-5b-cyprinol	3a,7a,12a-Trihydroxy-5b-cholestan-26-al	Not Available	VMH	9660774
MMDBr0004315	27-Deoxy-5b-cyprinol	3a,7a,12a-Trihydroxy-5b-cholestan-26-al	cytochrome P450, family 27, subfamily A, polypeptide 1	VMH	9660774
MMDBr0004340	Dihydroceramide	Ceramide (d18:1/18:0)	Not Available	VMH	10722759 10880336 11937514 8449895
MMDBr0004355	27-Hydroxycholesterol	7a-Hydroxy-cholestene-3-one	Not Available	VMH	0
MMDBr0004356	27-Hydroxycholesterol	7a-Hydroxy-cholestene-3-one	Not Available	VMH	0
MMDBr0004388	(S)-3-hydroxypalmitoleoyl-CoA	3-Oxopalmitoleoyl Coenzyme A	Not Available	VMH	11427448 7923814 8319713 9920399
MMDBr0004389	(S)-3-hydroxypalmitoleoyl-CoA	3-Oxopalmitoleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448 7923814 8319713 9920399
MMDBr0004390	(S)-3-hydroxypalmitoleoyl-CoA	3-Oxopalmitoleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448 7923814 8319713 9920399
MMDBr0004391	Cis-(3S)-Hydroxytetradec-7-Enoyl Coenzyme A	3-Oxomyrist-7-Enoyl Coenzyme A	Not Available	VMH	11427448 7923814 8319713 9920399
MMDBr0004392	Cis-(3S)-Hydroxytetradec-7-Enoyl Coenzyme A	3-Oxomyrist-7-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448 7923814 8319713 9920399
MMDBr0004393	Cis-(3S)-Hydroxytetradec-7-Enoyl Coenzyme A	3-Oxomyrist-7-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448 7923814 8319713 9920399
MMDBr0004394	3(S)-3-hydroxydodecen-(5Z)-oyl-CoA	3-Oxolaur-Cis-5-Enoyl Coenzyme A	Not Available	VMH	11427448
MMDBr0004395	3(S)-3-hydroxydodecen-(5Z)-oyl-CoA	3-Oxolaur-Cis-5-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448
MMDBr0004396	3(S)-3-hydroxydodecen-(5Z)-oyl-CoA	3-Oxolaur-Cis-5-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11427448
MMDBr0004420	3(S)-Hydroxy-Dihomo-Gama-Linolenoyl Coenzyme A	3-Oxo-Dihomo-Gama-Linolenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 10970790 7775433
MMDBr0004424	3(S)-Hydroxy-6Z,9Z,12Z-Octadecatrienoyl Coenzyme A	3-Oxo-6Z,9Z,12Z-Octadecatrienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 7775433
MMDBr0004437	(3S)-3-Hydroxy-cis-8-tetradecenoyl-CoA	3-Oxo-Cis-8-Tetradecenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 7775433
MMDBr0004439	Leukotriene B4	12-Oxo-Leukotriene B4	carbonyl reductase 1	VMH	11368003 9799565 9862787
MMDBr0004440	Leukotriene B4	12-Oxo-Leukotriene B4	dehydrogenase/reductase (SDR family) member 4	VMH	11368003 9799565 9862787
MMDBr0004441	Leukotriene B4	12-Oxo-Leukotriene B4	Not Available	VMH	11368003 9799565 9862787
MMDBr0004442	Leukotriene B4	12-Oxo-Leukotriene B4	dehydrogenase/reductase (SDR family) member 4	VMH	11368003 9799565 9862787
MMDBr0004443	20-Hydroxy-leukotriene B4	Aldehyde	alcohol dehydrogenase, iron containing, 1	VMH	11368003 9799565 9862787
MMDBr0004444	20-Hydroxy-leukotriene B4	Aldehyde	Not Available	VMH	11368003 9799565 9862787
MMDBr0004445	Aldehyde	20-Carboxy-leukotriene B4	aldehyde dehydrogenase 3 family, member A1	VMH	11368003 9799565 9862787
MMDBr0004446	Aldehyde	20-Carboxy-leukotriene B4	aldehyde dehydrogenase 1 family, member B1	VMH	11368003 9799565 9862787
MMDBr0004447	Aldehyde	20-Carboxy-leukotriene B4	aldehyde dehydrogenase 3 family, member A1	VMH	11368003 9799565 9862787
MMDBr0004480	13-cis-Retinal	all-trans-Retinoic acid	Not Available	VMH	10559215
MMDBr0004484	Pristanal	Pristanic acid	Not Available	VMH	11356164 9662422
MMDBr0004488	Pristanal	Pristanic acid	Not Available	VMH	11356164 9662422
MMDBr0004492	3(R)-Hydroxy-Pristanoyl Coenzyme A	Pristanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11060359
MMDBr0004497	3(R)-Hydroxy-(4R,8R,12R)-Trimethyl-Tridecanoyl Coenzyme A	3-Oxo-(4R,8R,12R)-Trimethyl-Tridecanoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11060359
MMDBr0004501	3(R)-Hydroxy-(2S,6R,10)-Trimethyl-Hendecanoyl Coenzyme A	3-Oxo-(2S,6R,10R)-Trimethyl-Hendecanoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11060359
MMDBr0004515	5-Androstenediol	Dihydrotestosterone	Not Available	VMH	10487690 11134149
MMDBr0004516	5-Androstenediol	Dihydrotestosterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	10487690 11134149
MMDBr0004517	5-Androstenediol	Dihydrotestosterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	10487690 11134149
MMDBr0004545	(3S)-Hydroxy-tetracosa-6,9,12,15,18,21-all-cis-hexaenoyl-CoA	3-Oxo-All-Cis-6,9,12,15,18,21-Tetracosahexaenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11734209
MMDBr0004560	3(S)-Hydroxy-Tetracosa-6,9,12,15,18-All-Cis-Pentaenoyl Coenzyme A	3-Oxo-All-Cis-6,9,12,15,18-Tetracosapentaenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11734209
MMDBr0004597	3(S)-Hydroxy-4(R),8-Dimethyl-Nonanoyl Coenzyme A	3-Oxo-4(R),8-Dimethyl-Nonanoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 9469587 9819701
MMDBr0004598	3(S)-Hydroxy-2(S),6-Dimethyl-Heptanoyl Coenzyme A	3-Oxo-(2S)-Methylisocapryloyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 9469587 9819701
MMDBr0004599	3(S)-Hydroxy-4-Methyl-Pentanoyl Coenzyme A	3-Oxo-4-Methyl-Pentanoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10407780 9469587 9819701
MMDBr0004610	L-Dopachrome	Leucodopachrome	Not Available	VMH	11744399
MMDBr0004661	24(R),25(R)-Varanoyl Coenzyme A	3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA	Not Available	VMH	10709654
MMDBr0004662	24(R),25(R)-Varanoyl Coenzyme A	3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10709654
MMDBr0004663	24(R),25(R)-Varanoyl Coenzyme A	3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	10709654
MMDBr0004715	3(S),12(R)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(R)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	hydroxysteroid (17-beta) dehydrogenase 10	VMH	7649996
MMDBr0004716	3(S),12(R)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(R)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7649996
MMDBr0004717	3(S),12(R)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(R)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7649996
MMDBr0004721	3(S),12(S)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(S)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	hydroxysteroid (17-beta) dehydrogenase 10	VMH	7649996
MMDBr0004722	3(S),12(S)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(S)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7649996
MMDBr0004723	3(S),12(S)-Dihydroxy-5-Oxo-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	3,5-Dioxo-12(S)-Hydroxy-Eicosa-8E,10E,14Z-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	7649996
MMDBr0004737	3a,7a,12a-Trihydroxy-5b-cholestanoic acid	3a,7a,12a-Trihydroxy-5b-cholestan-26-al	aldehyde dehydrogenase 3 family, member A1	VMH	1591235
MMDBr0004738	3a,7a,12a-Trihydroxy-5b-cholestanoic acid	3a,7a,12a-Trihydroxy-5b-cholestan-26-al	aldehyde dehydrogenase 1 family, member B1	VMH	1591235
MMDBr0004739	3a,7a,12a-Trihydroxy-5b-cholestanoic acid	3a,7a,12a-Trihydroxy-5b-cholestan-26-al	aldehyde dehydrogenase 3 family, member A1	VMH	1591235
MMDBr0004755	3(S),8(R)-Dihydroxy-6E,10Z-Hexadecadienoate	3-Oxo-8(R)-Hydroxy-Hexadeca-6E,10Z-Dienoate	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11356170
MMDBr0004761	3(S),6(R)-Dihydroxy-Tetradec-8Z-Enoate	3-Oxo-6(R)-Hydroxy-Tetradec-8-Cis-Enoate	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11356170
MMDBr0004765	3(S),8(S)-Dihydroxy-6E,10Z-Hexadecadienoate	3-Oxo-8(S)-Hydroxy-Hexadeca-6E,10Z-Dienoate	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11356170
MMDBr0004768	3(S),6(S)-Dihydroxy-Tetradec-8Z-Enoate	3-Oxo-6(S)-Hydroxy-Tetradec-8Z-Enoate	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11356170
MMDBr0004782	12-Oxo-Leukotriene B4	10,11-Dihydro-12-Oxo-Ltb4	carbonyl reductase 1	VMH	8244977 9862787
MMDBr0004783	12-Oxo-Leukotriene B4	10,11-Dihydro-12-Oxo-Ltb4	Not Available	VMH	8244977 9862787
MMDBr0004784	12-Oxo-Leukotriene B4	10,11-Dihydro-12-Oxo-Ltb4	Not Available	VMH	8244977 9862787
MMDBr0004811	3(S),5(S),12(R)-Trihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	3-Oxo-5(S),12(R)-Dihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	hydroxysteroid (17-beta) dehydrogenase 10	VMH	11368003 9862787
MMDBr0004812	3(S),5(S),12(R)-Trihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	3-Oxo-5(S),12(R)-Dihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11368003 9862787
MMDBr0004813	3(S),5(S),12(R)-Trihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	3-Oxo-5(S),12(R)-Dihydroxy-Eicosa-8-Trans-6,14-Cis-Trienoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	11368003 9862787
MMDBr0004911	20-Hydroxy-leukotriene E4	20-Oxo-Leukotriene E4	Not Available	VMH	12054595
MMDBr0004912	20-Oxo-Leukotriene E4	20-Cooh-Leukotriene E4	Not Available	VMH	12054595
MMDBr0004933	20 Coenzyme A-20-Oxo-18R-Hydroxyleucotriene B4	18,20-Dioxo-20 Coenzyme A-Leukotriene B4	hydroxysteroid (17-beta) dehydrogenase 10	VMH	12054595
MMDBr0004934	20 Coenzyme A-20-Oxo-18R-Hydroxyleucotriene B4	18,20-Dioxo-20 Coenzyme A-Leukotriene B4	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	12054595
MMDBr0004935	20 Coenzyme A-20-Oxo-18R-Hydroxyleucotriene B4	18,20-Dioxo-20 Coenzyme A-Leukotriene B4	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	12054595
MMDBr0004943	Coenzyme A-20-Cooh-18-Oxo-Lte4	18(R)-Hydroxy-20-Oxo-20 Coenzyme A-Lte4	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	12054595
MMDBr0004944	16,18-Oxo-18 Coenzyme A-Dinor-Lte4	16(S)-Hydroxy-18-Oxo-18 Coenzyme A-Lte4	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	12054595
MMDBr0005177	(2E)-Decenoyl-CoA	Octanoyl-CoA	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005178	(2E)-Decenoyl-CoA	Octanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005185	2,7-Decadienoyl Coenzyme A	5-Octenoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005186	2,7-Decadienoyl Coenzyme A	5-Octenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005192	Decanoyl-CoA (N-C10:0CoA)	Octanoyl-CoA	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005193	Decanoyl-CoA (N-C10:0CoA)	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	11411544 HMDB01070
MMDBr0005194	Sebacoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	15060085 9827430
MMDBr0005195	2,6,10-Trimethyl Undecanoyl Coenzyme A	4,8 Dimethylnonanoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	11591435
MMDBr0005196	Undecanoyl Coenzyme A	Nonanoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	18391478 HMDB00847
MMDBr0005197	5-Dodecenoyl Coenzyme A	3-Decenoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005198	(2E)-Dodecenoyl-CoA	Decanoyl-CoA (N-C10:0CoA)	acetyl-CoA acyltransferase 1	VMH	10709653 11296696 11330072 16766224
MMDBr0005200	2,6-Dodecadienoyl Coenzyme A	4-Decenoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005201	2,6,9-Dodecatrienoyl Coenzyme A	4,7-Decadienoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005202	2,6,9-Dodecatrienoyl Coenzyme A	4,7-Decadienoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530 20064629
MMDBr0005205	Lauroyl-CoA	Decanoyl-CoA (N-C10:0CoA)	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005206	Lauroyl-CoA	Decanoyl-CoA (N-C10:0CoA)	acetyl-CoA acyltransferase 1	VMH	11411544 HMDB06404
MMDBr0005208	Dodecanedioyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	15060085 9827430 20543534
MMDBr0005212	4,8,12-Trimethyltridecanoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	HMDB02221 11591435
MMDBr0005213	Tridecanoyl Coenzyme A	Undecanoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	18391478
MMDBr0005214	7-Tetradecenoyl Coenzyme A	5-Dodecenoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005215	5-Tetradecenoyl Coenzyme A	3Z-dodecenoyl-CoA	acetyl-CoA acyltransferase 1	VMH	10709653 11296696 11330072 16766224
MMDBr0005217	5,8,11-Tetradecatrienoyl Coenzyme A	3,6,9-Dodecatrienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005218	5,8,11-Tetradecatrienoyl Coenzyme A	3,6,9-Dodecatrienoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005219	Tetradecanoyl-CoA	Lauroyl-CoA	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005220	Tetradecanoyl-CoA	Lauroyl-CoA	acetyl-CoA acyltransferase 1	VMH	11411544
MMDBr0005222	Tetradecanedioyl Coenzyme A	Dodecanedioyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	15060085 9827430 HMDB02095 12651823
MMDBr0005224	Pristanoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	HMDB02396 11591435
MMDBr0005225	Pentadecanoyl Coenzyme A	Tridecanoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	18391478
MMDBr0005227	2-Hydroxyphytanoyl Coenzyme A	Formyl-CoA	aldehyde dehydrogenase 3 family, member A2	VMH	11591435
MMDBr0005228	Palmitoleyl-CoA	7-Tetradecenoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005229	7-Hexadecenoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	10709653 11296696 11330072 16766224
MMDBr0005230	7,10-Hexadecadienoyl Coenzyme A	5,8-Tetradecadienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005232	2,7,10-Hexadecatrienoyl Coenzyme A	5,8-Tetradecadienoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005233	7,10,13-Hexadecatrienoyl Coenzyme A	5,8,11-Tetradecatrienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005236	2,7,10-Hexadecatrienoyl Coenzyme A	5,8-Tetradecadienoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase/3-ketoacyl-CoA thiolase/enoyl-CoA hydratase (trifunctional protein), alpha subunit	VMH	20195903 20490924 17143551
MMDBr0005239	2,7,10,13-Hexadecatetraenoyl Coenzyme A	5,8,11-Tetradecatrienoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase/3-ketoacyl-CoA thiolase/enoyl-CoA hydratase (trifunctional protein), alpha subunit	VMH	20195903 20490924 17143551
MMDBr0005240	2,7,10,13-Hexadecatetraenoyl Coenzyme A	5,8,11-Tetradecatrienoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	7876265 20558530
MMDBr0005250	Palmityl-CoA	Tetradecanoyl-CoA	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005251	Palmityl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	11411544 7876265 HMDB01521
MMDBr0005253	Hexadecanedioyl Coenzyme A	Tetradecanedioyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	15060085 9827430
MMDBr0005256	Heptadecanoyl Coenzyme A	Pentadecanoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	18391478
MMDBr0005257	11-Octadecenoyl Coenzyme A	Palmitoleyl-CoA	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005258	oleoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	10709653 11296696 11330072 16766224 3821403
MMDBr0005260	Linoleoyl-CoA	7,10-Hexadecadienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH
MMDBr0005261	Gamma-linolenoyl-CoA	4,7,10-Hexadecatrienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005262	Alpha-Linolenoyl-CoA	7,10,13-Hexadecatrienoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005263	2,6,9,12-Octadecatetraenoyl Coenzyme A	4,7,10-Hexadecatrienoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase/3-ketoacyl-CoA thiolase/enoyl-CoA hydratase (trifunctional protein), alpha subunit	VMH	20195903 20490924 17143551
MMDBr0005264	2,6,9,12-Octadecatetraenoyl Coenzyme A	4,7,10-Hexadecatrienoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20064629 9799802
MMDBr0005265	Stearidonoyl CoA	4,7,10,13-Hexadecatetraenoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005266	Stearidonoyl CoA	4,7,10,13-Hexadecatetraenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005269	11-Eicosenoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	20626744 3821403
MMDBr0005270	2,5,8,11,14-Eicosapentaenoyl Coenzyme A	3,6,9,12-Octadecatetraenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20064629 9799802
MMDBr0005271	5,8,11,14,17-Eicosapentenoyl Coenzyme A	3,6,9,12,15-Octadecapentenoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005272	13-Docosenoyl Coenzyme A	11-Eicosenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20626744
MMDBr0005277	2,7,10,13,16,19-Docosahexenoyl Coenzyme A	5,8,11,14,17-Eicosapentenoyl Coenzyme A	acyl-CoA dehydrogenase, very long chain	VMH	20195903 20490924 17143551
MMDBr0005283	Docosanoyl-CoA	Eicosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	11124748
MMDBr0005286	Nervonyl CoA	13-Docosenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20626744
MMDBr0005287	Tetracosanoyl-CoA	Docosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	2117919
MMDBr0005291	Pentanoyl Coenzyme A	Propionyl-CoA	acetyl-CoA acyltransferase 2	VMH	10200137
MMDBr0005295	trans-2-Hexenoyl-CoA	Butyryl-CoA	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005296	trans-2-Hexenoyl-CoA	Butyryl-CoA	acetyl-CoA acyltransferase 1	VMH	20064629
MMDBr0005299	Hexanoyl-CoA	Butyryl-CoA	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005300	Hexanoyl-CoA	Butyryl-CoA	acetyl-CoA acyltransferase 1	VMH	11356164 HMDB01088
MMDBr0005301	Adipoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	15060085 9827430
MMDBr0005302	Heptanoyl Coenzyme A	Pentanoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	18391478
MMDBr0005303	5-Octenoyl Coenzyme A	3-Hexenoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005304	5-Octenoyl Coenzyme A	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005305	Octanoyl-CoA	Hexanoyl-CoA	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005306	Octanoyl-CoA	Hydrogen peroxide	acetyl-CoA acyltransferase 1	VMH	11411544 HMDB02845
MMDBr0005307	Suberyl Coenzyme A	Adipoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	15060085 9827430
MMDBr0005308	4,8 Dimethylnonanoyl Coenzyme A	2,6-Dimethylheptanoyl-CoA	Not Available	VMH	9469587 HMDB06258 9714723 11591435
MMDBr0005309	Nonanoyl Coenzyme A	Heptanoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	18391478 HMDB00666
MMDBr0005311	16-Hydroxy hexadecanoic acid	Hexadecanedioic acid	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	15060085 4062873
MMDBr0005312	W-Hydroxydocosanoicacid	Docosanedioicacid	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	15716582
MMDBr0005313	W-Hydroxydecanoicacid	Sebacic acid	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	P.L. Frabetti et al. On the narrow dip structure at 1.9 GeV/c2 in diffractive photoproduction. Physics Letters B, Volume 578, Issues 3-4, 2004, Pages 290-296. DOI
MMDBr0005316	Trans2,6Dodecadienoyl Coenzyme A	Trans4Decenoyl Coenzyme A	acetyl-CoA acyltransferase 2	VMH	20195903 20490924 17143551
MMDBr0005317	2,6-Dodecadienoyl Coenzyme A	4-Decenoyl Coenzyme A	acetyl-CoA acyltransferase 1	VMH	20558530
MMDBr0005498	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH	30371894
MMDBr0005717	Prostaglandin F2a	15-Keto-Prostaglandin F2A	hydroxyprostaglandin dehydrogenase 15-(NAD)	VMH	30371894
MMDBr0005718	Oxoadipic acid	2-Hydroxyadipic Acid	Not Available	VMH	30371894
MMDBr0005719	Phenyllactic acid	Phenylpyruvic acid	Not Available	VMH	30371894
MMDBr0005771	D-Arabitol	L-Threo-2-pentulose	Not Available	VMH	30371894
MMDBr0006133	Glycerol 3-phosphate	Dihydroxyacetone phosphate	Not Available	VMH	30371894
MMDBr0006819	16a-Hydroxyestrone	Estriol	Not Available	VMH	30371894
MMDBr0006895	Crotonoyl-CoA	Butyryl-CoA	Not Available	VMH	30371894
MMDBr0006903	1-Butanol	Butanal	Not Available	VMH	30371894
MMDBr0006942	L-Glutamic acid	Oxoglutaric acid	Not Available	VMH	30371894
MMDBr0006949	Hydroxypyruvic acid	L-Serine	Not Available	VMH	30371894
MMDBr0006955	MK-8	Menaquinol 8	Not Available	VMH	30371894
MMDBr0006956	2-Demethylmenaquinone 8	2-Demethylmenaquinol 8	Not Available	VMH	30371894
MMDBr0006958	Ketoleucine	Isovaleryl-CoA	Not Available	VMH	30371894
MMDBr0006959	3-Methyl-2-oxovaleric acid	2-Methylbutyryl-CoA	Not Available	VMH	30371894
MMDBr0006984	alpha-Ketoisovaleric acid	Isobutyryl-CoA	Not Available	VMH	30371894
MMDBr0006999	2-Octaprenyl-6-methoxyphenol	2-Octaprenyl-6-methoxy-1,4-benzoquinol	Not Available	VMH	30371894
MMDBr0007000	2-Octaprenylphenol	2-Octaprenyl-6-hydroxyphenol	Not Available	VMH	30371894
MMDBr0007002	(3S,5S)-3,5-Diaminocaproate	(S)-5-Amino-3-oxohexanoate	Not Available	VMH	30371894
MMDBr0007007	Oxoglutaric acid	2-Hydroxyglutarate	Not Available	VMH	30371894
MMDBr0007015	Succinic acid semialdehyde	Succinic acid	Not Available	VMH	30371894
MMDBr0007017	gamma-Hydroxybutyrate	Succinic acid semialdehyde	Not Available	VMH	30371894
MMDBr0007019	Butanal	Butyryl-CoA	Not Available	VMH	30371894
MMDBr0007028	Piperideine	5-Aminopentanoic acid	Not Available	VMH	30371894
MMDBr0007030	Glutarate semialdehyde	Glutaric acid	Not Available	VMH	30371894
MMDBr0007034	Cob(II)yrinate a,c diamide	Cob(I)yrinate a,c diamide	Not Available	VMH	30371894
MMDBr0007035	L-Threonine	L-2-Amino-3-oxobutanoic acid	Not Available	VMH	30371894
MMDBr0007036	Aminoacetone	1-Amino-2-propanol	Not Available	VMH	30371894
MMDBr0007039	Aminoacetaldehyde	Glycine	Not Available	VMH	30371894
MMDBr0007070	L-Histidinol	L-Histidine	Not Available	VMH	30371894
MMDBr0007074	3-Carboxy-2-hydroxy-4-methylpentanoate	3-Carboxy-4-methyl-2-oxopentanoate	Not Available	VMH	30371894
MMDBr0007078	Lactaldehyde	(S)-Propane-1,2-diol	Not Available	VMH; KEGG	30371894
MMDBr0007119	L-Arogenate	L-Tyrosine	Not Available	VMH	30371894
MMDBr0007178	L-Aspartic acid	Iminoaspartate	Not Available	VMH	30371894
MMDBr0007179	D-Biotin D-sulfoxide	Biotin	Not Available	VMH	30371894
MMDBr0007206	L-D-1-Pyrroline-5-carboxylic acid	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0007209	Prephenate	4-Hydroxyphenylpyruvic acid	Not Available	VMH	30371894
MMDBr0007214	L-Glutamic-gamma-semialdehyde	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0007259	D-Glyceraldehyde	Glycerol	Not Available	VMH	30371894
MMDBr0007260	Ethanol	Acetaldehyde	Not Available	VMH; KEGG	30371894
MMDBr0007314	4a-Carbinolamine tetrahydrobiopterin	L-erythro-tetrahydrobiopterin	Not Available	VMH	30371894
MMDBr0007317	1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate	Dimethylallylpyrophosphate	Not Available	VMH	30371894
MMDBr0007327	D-Erythrose 4-phosphate	4-Phospho-D-erythronate	Not Available	VMH	30371894
MMDBr0007414	Glycerol 3-phosphate	Dihydroxyacetone phosphate	Not Available	VMH	30371894
MMDBr0007423	Glyceraldehyde 3-phosphate	Glyceric acid 1,3-biphosphate	Not Available	VMH; KEGG	30371894
MMDBr0007470	Inosinic acid	Xanthylic acid	Not Available	VMH; KEGG	30371894
MMDBr0007472	1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate	Isopentenyl pyrophosphate	Not Available	VMH	30371894
MMDBr0007485	2-C-Methyl-D-erythritol 2,4-cyclodiphosphate	1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate	Not Available	VMH	30371894
MMDBr0007495	Thymidine 5'-triphosphate	dTDP	Not Available	VMH	30371894
MMDBr0007520	3-Phospho-D-glycerate	Phosphohydroxypyruvic acid	Not Available	VMH	30371894
MMDBr0007526	O-Phospho-4-hydroxy-L-threonine	2-Amino-3-oxo-4-phosphonooxybutyrate	Not Available	VMH	30371894
MMDBr0007650	Nicotinic acid adenine dinucleotide	L-Glutamic acid	Not Available	VMH; KEGG	30371894
MMDBr0007665	Methanol	Formaldehyde	Not Available	VMH; KEGG	30371894
MMDBr0007666	Formaldehyde	Formic acid	Not Available	VMH	30371894
MMDBr0007669	Glycolaldehyde	Glycolic acid	Not Available	VMH; KEGG	30371894
MMDBr0007670	Glycolic acid	Glyoxylic acid	Not Available	VMH	30371894
MMDBr0007672	2-Hydroxy-3-oxopropanoate	Glyceric acid	Not Available	VMH	30371894
MMDBr0007680	3-Hydroxyphenylacetic acid	3,4-Dihydroxybenzeneacetic acid	Not Available	VMH	30371894
MMDBr0007681	5-Carboxymethyl-2-hydroxymuconate semialdehyde	5-Carboxymethyl-2-hydroxymuconate	Not Available	VMH	30371894
MMDBr0007682	p-Hydroxyphenylacetic acid	3,4-Dihydroxybenzeneacetic acid	Not Available	VMH	30371894
MMDBr0007690	4-Aminobutyraldehyde	gamma-Aminobutyric acid	Not Available	VMH; KEGG	30371894
MMDBr0007693	trans-2-Hexenoyl-CoA	Hexanoyl-CoA	Not Available	VMH	30371894
MMDBr0007694	(2E)-Decenoyl-CoA	Decanoyl-CoA (N-C10:0CoA)	Not Available	VMH	30371894
MMDBr0007695	(2E)-Dodecenoyl-CoA	Lauroyl-CoA	Not Available	VMH	30371894
MMDBr0007696	trans-tetradec-2-enoyl-CoA	Tetradecanoyl-CoA	Not Available	VMH	30371894
MMDBr0007697	(2E)-Hexadecenoyl-CoA	Palmityl-CoA	Not Available	VMH	30371894
MMDBr0007709	Acetaldehyde	Acetic acid	Not Available	VMH; KEGG	30371894
MMDBr0007730	(R)-3-Hydroxybutyric acid	Acetoacetic acid	Not Available	VMH	30371894
MMDBr0007735	Cob(I)alamin	Cob(II)alamin	Not Available	VMH	30371894
MMDBr0007753	2,3-Diketo-L-gulonate	3-Dehydro-L-gulonate	Not Available	VMH	30371894
MMDBr0007832	Galactitol 1-phosphate	D-Tagatose 6-phosphate	Not Available	VMH	30371894
MMDBr0007836	Glyoxylic acid	Oxalic acid	Not Available	VMH	30371894
MMDBr0007841	Glycerol	Dihydroxyacetone	Not Available	VMH	30371894
MMDBr0007854	Acetoacetyl-CoA	3-Hydroxybutyryl-CoA	Not Available	VMH	30371894
MMDBr0007855	3-Oxooctanoyl-CoA	(S)-3-Hydroxyoctanoyl-CoA	Not Available	VMH	30371894
MMDBr0007856	3-Oxodecanoyl-CoA	(S)-Hydroxydecanoyl-CoA	Not Available	VMH	30371894
MMDBr0007857	3-Oxododecanoyl-CoA	(S)-3-Hydroxydodecanoyl-CoA	Not Available	VMH	30371894
MMDBr0007858	3-Oxotetradecanoyl-CoA	(S)-3-Hydroxytetradecanoyl-CoA	Not Available	VMH	30371894
MMDBr0007859	3-Oxohexadecanoyl-CoA	(S)-3-Hydroxyhexadecanoyl-CoA	Not Available	VMH	30371894
MMDBr0007860	2-Methyl-3-hydroxybutyryl-CoA	2-Methylacetoacetyl-CoA	Not Available	VMH	30371894
MMDBr0007861	(3S)-3-Hydroxyadipyl-CoA	3-Oxoadipyl-CoA	Not Available	VMH	30371894
MMDBr0007866	(S)-3-Hydroxyisobutyric acid	2-Methyl-3-oxopropanoic acid	Not Available	VMH	30371894
MMDBr0007878	Imidazole-4-acetaldehyde	Imidazoleacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0007884	Lactaldehyde	L-Lactic acid	Not Available	VMH; KEGG	30371894
MMDBr0007900	(S)-malate(2-)	Oxalacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0007909	2-Methyl-3-oxopropanoic acid	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0007910	Propanal	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0007919	Nitric oxide	Nitrate	Not Available	VMH	30371894
MMDBr0007935	Dihydrolipoamide	Lipoamide	Not Available	VMH	30371894
MMDBr0007962	D-Sorbitol 6-phosphate	Fructose 6-phosphate	Not Available	VMH	30371894
MMDBr0007988	UDP-N-Acetyl-D-mannosamine	UDP-N-Acetyl-D-mannosaminouronate	Not Available	VMH	30371894
MMDBr0007990	Uridine diphosphate glucose	UDP-Glucuronic acid	Not Available	VMH	30371894
MMDBr0007995	(-)-Ureidoglycolate	Oxalureate	Not Available	VMH	30371894
MMDBr0008014	D-Glyceraldehyde	Glyceric acid	Not Available	VMH	30371894
MMDBr0008016	5-Methyltetrahydrofolic acid	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0008035	1-Deoxy-D-xylulose 5-phosphate	Pyridoxine 5'-phosphate	Not Available	VMH	30371894
MMDBr0008036	Pyridoxine 5'-phosphate	Pyridoxal 5'-phosphate	Not Available	VMH	30371894
MMDBr0008043	5-Aminoimidazole ribonucleotide	4-Amino-2-methyl-5-phosphomethylpyrimidine	Not Available	VMH	30371894
MMDBr0008083	3-Hydroxypropanal	propane-1,3-diol	Not Available	VMH	30371894
MMDBr0008099	Glyoxylic acid	Glycolic acid	Not Available	VMH	30371894
MMDBr0008100	Hydroxypyruvic acid	Glyceric acid	Not Available	VMH	30371894
MMDBr0008120	Glycolaldehyde	Glycolic acid	Not Available	VMH	30371894
MMDBr0008135	5,10-Methylene-THF	5,10-Methenyltetrahydrofolic acid	Not Available	VMH	30371894
MMDBr0008141	2-Ketobutyric acid	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0008143	3-(3-Hydroxyphenyl)propionate	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894
MMDBr0008149	Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894
MMDBr0008162	Flavin mononucleotide	Reduced FMN	Not Available	VMH	30371894
MMDBr0008171	Melilotate	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894
MMDBr0008174	Phenylpropanoate	Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol	Not Available	VMH	30371894
MMDBr0008176	D-Altronate	D-Tagaturonate	Not Available	VMH	30371894
MMDBr0008183	(R)-acetoin	Acetaldehyde	Not Available	VMH	30371894
MMDBr0008192	Hypoxanthine	Xanthine	Not Available	VMH; KEGG	30371894
MMDBr0008193	Isocitric acid	Oxoglutaric acid	Not Available	VMH	30371894
MMDBr0008222	D-Phenyllactic acid	Phenylpyruvic acid	Not Available	VMH	30371894
MMDBr0008223	L-Tryptophan	Indole-3-propionate	Not Available	VMH	30371894
MMDBr0008224	Glycine	Acetyl phosphate	Not Available	VMH	30371894
MMDBr0008225	D-Proline	5-Aminopentanoic acid	Not Available	VMH	30371894
MMDBr0008226	Ketoleucine	Isovaleric acid	Not Available	VMH	30371894
MMDBr0008227	alpha-Ketoisovaleric acid	Isobutyric acid	Not Available	VMH	30371894
MMDBr0008228	3-Methyl-2-oxovaleric acid	Ethylmethylacetic acid	Not Available	VMH	30371894
MMDBr0008229	Betaine	Acetyl phosphate	Not Available	VMH	30371894
MMDBr0008237	(S)-3-Hydroxyisobutyric acid	(S)-Methylmalonic acid semialdehyde	Not Available	VMH	30371894
MMDBr0008238	(S)-Methylmalonic acid semialdehyde	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0008239	(R)-acetoin	Diacetyl	Not Available	VMH	30371894
MMDBr0008240	Betaine aldehyde	Betaine	Not Available	VMH; KEGG	30371894
MMDBr0008242	(2R,3R)-2,3-Butanediol	(R)-acetoin	Not Available	VMH	30371894
MMDBr0008243	Choline	Betaine aldehyde	Not Available	VMH; KEGG	30371894
MMDBr0008258	3-Hydroxyadipyl-CoA	3-Oxoadipyl-CoA	Not Available	VMH	30371894
MMDBr0008291	Glycine	5,10-Methylene-THF	Not Available	VMH	30371894
MMDBr0008308	D-Mannitol	D-Fructose	Not Available	VMH	30371894
MMDBr0008319	Benzoic acid	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate	Not Available	VMH	30371894
MMDBr0008321	Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate	Pyrocatechol	Not Available	VMH	30371894
MMDBr0008332	Nitrous oxide	Nitrogen	Not Available	VMH	30371894
MMDBr0008335	Nitrate	Nitrite	Not Available	VMH	30371894
MMDBr0008344	D-Arabitol	D-Xylulose	Not Available	VMH	30371894
MMDBr0008356	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	VMH	30371894
MMDBr0008392	MK-8	Menaquinol 8	Not Available	VMH	30371894
MMDBr0008393	2-Demethylmenaquinone 8	2-Demethylmenaquinol 8	Not Available	VMH	30371894
MMDBr0008394	(S)-2,3-epoxysqualene	squalene	Not Available	VMH	30371894
MMDBr0008399	L-Leucine	Ketoleucine	Not Available	VMH	30371894
MMDBr0008400	L-Isoleucine	3-Methyl-2-oxovaleric acid	Not Available	VMH	30371894
MMDBr0008402	L-Valine	alpha-Ketoisovaleric acid	Not Available	VMH	30371894
MMDBr0008413	Tetrahydrofolic acid	Folic acid	Not Available	VMH	30371894
MMDBr0008432	Ribitol	D-Ribulose	Not Available	VMH	30371894
MMDBr0008438	Succinyl-CoA	Oxoglutaric acid	Not Available	VMH	30371894
MMDBr0008461	Oxoglutaric acid	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0008469	3-Hydroxy-3-methylglutaryl-CoA	Mevalonic acid	Not Available	VMH	30371894
MMDBr0008475	L-Tyrosine	Desaminotyrosine	Not Available	VMH	30371894
MMDBr0008493	L-Pipecolic acid	1-Piperideine-2-carboxylic acid	Not Available	VMH	30371894
MMDBr0008530	Crotonoyl-CoA	Butyryl-CoA	Not Available	VMH	30371894
MMDBr0008559	4-Fumarylacetoacetic acid	Succinyl-Acetoacetate	Not Available	VMH	30371894
MMDBr0008560	Maleylacetoacetic acid	Succinyl-Acetoacetate	Not Available	VMH	30371894
MMDBr0008565	Vanilpyruvic Acid	Vanil-Lactate	Not Available	VMH	30371894
MMDBr0008573	3-Methyl-2-oxovaleric acid	2-Hydroxy-3-methylpentanoic acid	lactate dehydrogenase A	VMH	30371894
MMDBr0008576	alpha-Ketoisovaleric acid	2-Hydroxy-3-methylbutyric acid	lactate dehydrogenase A	VMH	30371894
MMDBr0008586	2-Methyl-3-Oxo-Valerate	2-Methyl-3-Hydroxy-Valerate	Not Available	VMH	30371894
MMDBr0008662	Succinic acid semialdehyde	gamma-Hydroxybutyrate	Not Available	VMH	30371894
MMDBr0009084	2,3-Dihydro-1H-Indole-5,6-Dione	Leukoaminochrome	NAD(P)H dehydrogenase, quinone 1	VMH	30371894
MMDBr0009371	Oxoglutaric acid	2-Hydroxyglutarate	phosphoglycerate dehydrogenase	VMH; KEGG	30371894
MMDBr0009407	15S-Hydroxy-5Z,8Z,11Z,13E-Eicosatetraenoic Acid	15-KETE	Not Available	VMH; KEGG	30371894
MMDBr0009429	11,12-Epoxyeicosatrienoic acid	9,10-Epoxy-12Z-Octadecenoic Acid	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0009430	9,10-Epoxy-12Z-Octadecenoic Acid	7,8-Epoxy-(4Z,10Z)-Hexadecadienoic Acid	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0009431	7,8-Epoxy-(4Z,10Z)-Hexadecadienoic Acid	5,6-Epoxy-(8Z)-Tetradecenoic Acid	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0009432	10,11-Epoxy-(4Z,7Z)-Hexadecadienoic Acid	8,9-Epoxy-(5Z)-Tetradecenoic Acid	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0009434	12-Hydroxyeicosatetraenoate	12R-Hydroxy-5Z,8Z,12Z-Eicosatrienoic Acid	hydroxysteroid (17-beta) dehydrogenase 12	VMH	30371894
MMDBr0009443	15-Oxo-Lipoxin A4	Lipoxin A4	hydroxyprostaglandin dehydrogenase 15-(NAD)	VMH	30371894
MMDBr0009451	20-Hydroxy-leukotriene B4	Aldehyde	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH	30371894
MMDBr0009480	20-Carboxy-leukotriene B4	18-Carboxy Dinor Leukotriene B4	Not Available	VMH	30371894
MMDBr0009497	11-Dehydrothromboxane B2	Thromboxane B2	Not Available	VMH; KEGG	30371894
MMDBr0009499	6-Ketoprostaglandin E1	6-Keto-prostaglandin F1a	Not Available	VMH	30371894
MMDBr0009500	6-Keto-prostaglandin F1a	Prostaglandin F1a	Not Available	VMH	30371894
MMDBr0009502	Prostaglandin F2a	Prostaglandin H2	aldo-keto reductase family 1, member C3	VMH; KEGG	30371894
MMDBr0009503	9S,11R-Dihydroxy-15-Oxo-5Z,13E-Prostadienoic Acid	Prostaglandin F2a	Not Available	VMH; KEGG	30371894
MMDBr0009534	4beta-methylzymosterol-4alpha-carboxylic acid	3-Keto-4-methylzymosterol	NAD(P) dependent steroid dehydrogenase-like	VMH	30371894
MMDBr0009545	Lathosterol	7-Dehydrocholesterol	sterol-C5-desaturase	VMH; KEGG	30371894
MMDBr0009563	3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA	3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA	hydroxysteroid (17-beta) dehydrogenase 4	VMH	30371894
MMDBr0009568	(24S)-7Alpha,24-Dihydroxycholesterol	7Alpha,24-Dihydroxycholest-4-En-3-One	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 7	VMH	30371894
MMDBr0009596	7Alpha,25-Dihydroxycholest-4-En-3-One	7-a,25-Dihydroxycholesterol	Not Available	VMH	30371894
MMDBr0009611	21-Hydroxypregnenolone	Deoxycorticosterone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH; KEGG	30371894
MMDBr0009615	17alpha,21-Dihydroxypregnenolone	Cortexolone	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH; KEGG	30371894
MMDBr0009616	11b,17a,21-Trihydroxypreg-nenolone	Cortisol	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH; KEGG	30371894
MMDBr0009619	Dehydroepiandrosterone	androst-5-ene-3,17-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009620	Dehydroepiandrosterone	androst-5-ene-3,17-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009622	Pregnenolone	pregn-5-ene-3,20-dione	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009625	17a-Hydroxypregnenolone	pregn-5-ene-3,20-dione-17-ol	hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	VMH	30371894
MMDBr0009638	Androstanedione	Androsterone	aldo-keto reductase family 1, member C1	VMH; KEGG	30371894
MMDBr0009663	23S,25-dihydroxyvitamin D3	23S,25,26-Trihydroxyvitamin D3	coenzyme Q6 monooxygenase	VMH	30371894
MMDBr0009664	Secalciferol	24-Hydroxycalcitriol	cytochrome P450, family 24, subfamily A, polypeptide 1	VMH	30371894
MMDBr0009665	Secalciferol	24-Hydroxycalcitriol	cytochrome P450, family 24, subfamily A, polypeptide 1	VMH	30371894
MMDBr0010008	12Z,15Z,18Z,21Z-Tetracosatetraenoyl Coenzyme A	Hydrogen peroxide	Not Available	VMH	30371894
MMDBr0010009	(9Z,12Z,15Z,18Z,21Z)-Tetracosapentaenoyl Coenzyme A	Hydrogen peroxide	Not Available	VMH	30371894
MMDBr0010010	Tetracosatetraenoyl CoA	Hydrogen peroxide	Not Available	VMH	30371894
MMDBr0010011	Tricosanoyl Coenzyme A	Hydrogen peroxide	Not Available	VMH	30371894
MMDBr0010014	(S)-3-hydroxyhexacosanoyl-CoA	3-oxohexacosanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010017	3-hydroxytetracosanoyl-CoA	3-oxotetracosanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010021	3-hydroxydocosanoyl-CoA	3-oxodocosanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010025	3-hydroxyicosanoyl-CoA	3-oxoicosanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010029	3-hydroxyoctadecanoyl-CoA	3-Oxooctadecanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010032	(S)-Hydroxyoctanoyl-CoA	3-Oxooctanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010036	(S)-Hydroxyhexanoyl-CoA	3-Oxohexanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010042	3-hydroxydocosanoyl-CoA	3-oxodocosanoyl-CoA	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010046	3-hydroxyicosanoyl-CoA	3-oxoicosanoyl-CoA	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010050	3-hydroxyoctadecanoyl-CoA	3-Oxooctadecanoyl-CoA	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010060	3-Hydroxyheneicosanoyl Coenzyme A	3-Oxoheneicosanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010064	3-Hydroxynonadecanoyl Coenzyme A	3-Oxononadecanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010068	3-Hydroxyheptadecanoyl Coenzyme A	3-Oxoheptadecanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010072	3-Hydroxypentadecanoyl Coenzyme A	3-Oxopentadecanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010076	3-Hydroxytridecanoyl Coenzyme A	3-Oxotridecanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010080	3-Hydroxyundecanoyl Coenzyme A	3-Oxoundecanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010084	3-Hydroxynonanoyl Coenzyme A	3-Oxononanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010088	3-Hydroxyheptanoyl Coenzyme A	3-Oxoheptanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010092	3-Hydroxypentanoyl Coenzyme A	3-Oxopentanoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010096	3(S)-Hydroxy-13Cis-Docosenoyl Coenzyme A	3-Oxo-13Cis-Docosenoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010100	3(S)-Hydroxy-11-Cis-Eicosenoyl Coenzyme A	3-Oxo-11-Cis-Eicosenoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010105	(S)-3-Hydroxy-7-Hexadecenoyl Coenzyme A	3-Oxo-7-Hexadecenoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010109	Cis-(3S)-Hydroxytetradec-5-Enoyl Coenzyme A	3-Oxomyrist-5-Enoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010113	3(S)-Hydroxy-13-Cis-Eicosenoyl Coenzyme A	3-Oxo-13-Cis-Eicosenoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010117	(S)-3-Hydroxy-11-Cis-Octadecenoyl Coenzyme A	3-oxo-11-cis-octadecenoyl-CoA	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010121	trans-Delta2, cis-delta4-decadienoyl-CoA	3-Decenoyl Coenzyme A	2,4-dienoyl CoA reductase 1, mitochondrial	VMH	30371894
MMDBr0010124	trans-Delta2, cis-delta4-decadienoyl-CoA	3-Decenoyl Coenzyme A	2,4-dienoyl CoA reductase 1, mitochondrial	VMH	30371894
MMDBr0010127	3(S)-Hydroxy-Hexacosenoyl Coenzyme A	3-oxohexacosanoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010131	3(S)-Hydroxy-Cis-15-Tetracosaenoyl Coenzyme A	3-Oxo-Cis-15-Tetracosaenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010135	3(S)-Hydroxy-13Cis-Docosenoyl Coenzyme A	3-Oxo-13Cis-Docosenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010139	3(S)-Hydroxy-11-Cis-Eicosenoyl Coenzyme A	3-Oxo-11-Cis-Eicosenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010143	(S)-3-Hydroxyoleyleoyl Coenzyme A	3-Oxooleoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010147	(S)-3-Hydroxy-7-Hexadecenoyl Coenzyme A	3-Oxo-7-Hexadecenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010151	Cis-(3S)-Hydroxytetradec-5-Enoyl Coenzyme A	3-Oxomyrist-5-Enoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010155	3(S)-Hydroxy-13-Cis-Eicosenoyl Coenzyme A	3-Oxo-13-Cis-Eicosenoyl Coenzyme A	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010159	(S)-3-Hydroxy-11-Cis-Octadecenoyl Coenzyme A	3-oxo-11-cis-octadecenoyl-CoA	enoyl-CoA, hydratase/3-hydroxyacyl CoA dehydrogenase	VMH	30371894
MMDBr0010162	10Z-Heptadecenoyl Coenzyme A	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0010163	9Z-Heptadecenoyl Coenzyme A	Propionyl-CoA	Not Available	VMH	30371894
MMDBr0010186	3(S)-Hydroxy-Dihomo-Gama-Linolenoyl Coenzyme A	3-Oxo-Dihomo-Gama-Linolenoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010190	3(S)-Hydroxy-6Z,9Z,12Z-Octadecatrienoyl Coenzyme A	3-Oxo-6Z,9Z,12Z-Octadecatrienoyl Coenzyme A	hydroxyacyl-CoA dehydrogenase	VMH	30371894
MMDBr0010270	L-Cystine	L-Cysteine	Not Available	VMH; KEGG	30371894
MMDBr0010296	Choline	Betaine aldehyde	choline dehydrogenase	VMH; KEGG	30371894
MMDBr0010302	Biliverdin	Bilirubin	biliverdin reductase A	VMH; KEGG	30371894
MMDBr0010311	Alpha-Lactose	3'-Ketolactose	Not Available	VMH; KEGG	30371894
MMDBr0010336	(R)-Lipoic acid	Dihydrolipoamide	dihydrolipoamide dehydrogenase	VMH	30371894
MMDBr0010341	13'-Carboxy-Alpha-Tocotrienol	11'-Carboxy-alpha-tocotrienol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010342	11'-Carboxy-alpha-tocotrienol	9'-Carboxy-alpha-tocotrienol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010343	9'-Carboxy-alpha-tocotrienol	7'-Carboxy-alpha-tocotrienol	Not Available	VMH	30371894
MMDBr0010344	7'-Carboxy-alpha-tocotrienol	5-Carboxy-Alpha-Chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010345	5-Carboxy-Alpha-Chromanol	Alpha-CEHC	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010353	13'-Carboxy-Gama-Tocotrienol	11'-Carboxy-gamma-tocotrienol	Not Available	VMH	30371894
MMDBr0010354	9'-Carboxy-gamma-tocotrienol	7'-Carboxy-gamma-tocotrienol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010355	7'-Carboxy-gamma-tocotrienol	5'-Carboxy-gamma-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010356	5'-Carboxy-gamma-chromanol	gamma-CEHC	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010363	13'-Carboxy-Gama-Tocopherol	11'-Carboxy-gamma-chromanol	Not Available	VMH	30371894
MMDBr0010364	11'-Carboxy-gamma-chromanol	9'-Carboxy-gamma-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010365	9'-Carboxy-gamma-chromanol	7'-Carboxy-gamma-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010366	7'-Carboxy-gamma-chromanol	5'-Carboxy-gamma-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010370	13'-Carboxy-Alpha-Tocopherol	11'-Carboxy-alpha-chromanol	Not Available	VMH	30371894
MMDBr0010371	11'-Carboxy-alpha-chromanol	9'-Carboxy-alpha-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010372	9'-Carboxy-alpha-chromanol	7'-Carboxy-alpha-chromanol	aminoadipate-semialdehyde dehydrogenase	VMH	30371894
MMDBr0010373	7'-Carboxy-alpha-chromanol	5-Carboxy-Alpha-Chromanol	Not Available	VMH	30371894
MMDBr0010392	Vitamin A	Retinal	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH; KEGG	30371894
MMDBr0010394	Retinal	all-trans-Retinoic acid	aldehyde dehydrogenase 1 family, member A1	VMH; KEGG	30371894
MMDBr0010414	4-Hydroxyphenylpyruvic acid	Hydroxyphenyllactic acid	Not Available	VMH; KEGG	30371894
MMDBr0010416	4-Coumaroyl-CoA	4-hydroxybenzoyl-CoA	Not Available	VMH; KEGG	30371894
MMDBr0010418	4-Hydroxyphenylacetaldehyde	p-Hydroxyphenylacetic acid	aldehyde dehydrogenase 1 family, member A3	VMH	30371894
MMDBr0010491	Chloral hydrate	2,2,2-Trichloroethanol	alcohol dehydrogenase 1A (class I), alpha polypeptide	VMH; KEGG	30371894
MMDBr0010754	Vitamin K1	Phylloquinol	NAD(P)H dehydrogenase, quinone 1	VMH; KEGG	30371894
MMDBr0010838	N-Acetylneuraminic acid	N-Glycolylneuraminic acid	Not Available	VMH; KEGG	30371894
MMDBr0010852	L-Histidinol	L-Histidinal	Not Available	VMH	30371894
MMDBr0010853	L-Histidinal	L-Histidine	Not Available	VMH	30371894
MMDBr0010888	Riboflavin	Reduced riboflavin	Not Available	VMH	30371894
MMDBr0010890	6-Phosphogluconic acid	D-Ribulose 5-phosphate	Not Available	VMH	30371894
MMDBr0010903	Hydroxymethylglutathione	S-Formylglutathione	Not Available	VMH	30371894
MMDBr0010924	gamma-Butyrobetainyl-CoA	Crotonobetainyl-CoA	Not Available	VMH	30371894
MMDBr0010927	Glycolaldehyde	1,2-Ethanediol	Not Available	VMH	30371894
MMDBr0010928	D-Lactaldehyde	Propylene glycol	Not Available	VMH	30371894
MMDBr0010934	squalene	(S)-2,3-epoxysqualene	Not Available	VMH	30371894
MMDBr0010944	D-Glyceraldehyde	Glyceric acid	Not Available	VMH	30371894
MMDBr0010959	D-Erythro-3-Methylmalate	2-Ketobutyric acid	Not Available	VMH	30371894
MMDBr0010977	Saccharopine	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0010985	Riboflavin	Reduced riboflavin	Not Available	VMH	30371894
MMDBr0010992	Saccharopine	Oxoglutaric acid	Not Available	VMH	30371894
MMDBr0010999	2-Methyl-3-oxopropanoic acid	R-Methylmalonyl-CoA	Not Available	VMH	30371894
MMDBr0012614	Ubiquinone-1	Ubiquinol-10	mitochondrially encoded NADH dehydrogenase 1	VMH	30371894
MMDBr0012634	Cholic acid	3-Dehydrocholic acid; 3oxo-7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid	Not Available	VMH	30371894
MMDBr0012636	Cholesterol	5beta-Coprostanol	Not Available	VMH	30371894
MMDBr0012649	Isochenodeoxycholic acid; 3beta,7alpha,12alpha-Trihydroxy-5beta-cholanic acid	3-Dehydrocholic acid; 3oxo-7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic acid	Not Available	VMH	30371894
MMDBr0012684	Ketoleucine	Isovaleryl-CoA	Not Available	VMH	30371894
MMDBr0012689	Cholesterol	5beta-Coprostanol	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Pellagra	Slight Increase	Association	Human Blood	HMDB	17709435

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	742	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Human supragingival plaque; Goat feces; Sheep feces; Human subgingival plaque; Human saliva; River trout ; Cattle ; Rat ; Turkey ; Sheep ; Dog ; Lion ; Chicken ; American dog tick ; Human mucosa	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	565	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish ; Goat feces; Sheep feces	Metabolic reconstruction
Bacteria	Actinobacteria	235	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	139	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human supragingival plaque; Human subgingival plaque; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	19	Human feces; Human ; Pig ; Relapsing fever tick	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	12	Human feces; Human	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	25	Human feces; Human ; Goat ; Pig	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	120	Human feces; Human saliva; Human supragingival plaque	Unknown
Archaea/Archaea	Crenarchaeota	22	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	19	Human feces
Bacteria	Aquificae	5
Archaea/Archaea	Euryarchaeota	44	Human feces; Human	Metabolic reconstruction
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Archaea/Archaea	nah	11
Eukaryota/Fungi	Mucoromycota	4
Bacteria	Deinococcus-thermus	8
Bacteria	Thermotogae	10
Bacteria	Cyanobacteria	24
Bacteria	nah	5	Human
Bacteria	Acidobacteria	3
Bacteria	Chlorobi	12
Bacteria	Chloroflexi	9
Bacteria	Dictyoglomi	2
Archaea/Archaea	Korarchaeota	1
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria	Elusimicrobia	1
Bacteria	Nitrospirae	1
Archaea	nah	2
Bacteria	Gemmatimonadetes	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified								HMDB
Human Blood	Detected and Quantified	0.0036			uM	Infant (0-1 year old)	Female	Nicotinamide Adenine Dinucleotide Deficiency	HMDB	28792876
Human Blood	Detected and Quantified	29.1	25.0	33.2	uM	Adult (>18 years old)	Both	Pellagra	HMDB	17709435
Human Cellular cytoplasm	Detected and Quantified	88.7			uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Blood	Detected and Quantified	24.3	23.0	25.6	uM	Adult (>18 years old)	Both	Normal	HMDB	17709435
Human Adrenal gland	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000902

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15846

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kunsman GW, Manno JE, Cockerham KR, Manno BR: A modification and validation of two urine ethanol procedures for use with the Monarch 2000 Chemistry System. J Anal Toxicol. 1991 May-Jun;15(3):130-5. doi: 10.1093/jat/15.3.130. [PubMed:1943056 ]
Krotz F, Sohn HY, Gloe T, Zahler S, Riexinger T, Schiele TM, Becker BF, Theisen K, Klauss V, Pohl U: NAD(P)H oxidase-dependent platelet superoxide anion release increases platelet recruitment. Blood. 2002 Aug 1;100(3):917-24. doi: 10.1182/blood.v100.3.917. [PubMed:12130503 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Hamza A, Cho H, Tai HH, Zhan CG: Understanding human 15-hydroxyprostaglandin dehydrogenase binding with NAD+ and PGE2 by homology modeling, docking and molecular dynamics simulation. Bioorg Med Chem. 2005 Jul 15;13(14):4544-51. doi: 10.1016/j.bmc.2005.04.053. [PubMed:15908215 ]
Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. doi: 10.1016/j.jmb.2005.05.014. [PubMed:15946682 ]
Begonja AJ, Gambaryan S, Geiger J, Aktas B, Pozgajova M, Nieswandt B, Walter U: Platelet NAD(P)H-oxidase-generated ROS production regulates alphaIIbbeta3-integrin activation independent of the NO/cGMP pathway. Blood. 2005 Oct 15;106(8):2757-60. doi: 10.1182/blood-2005-03-1047. Epub 2005 Jun 23. [PubMed:15976180 ]
Orczyk J, Morre DM, Morre DJ: Periodic fluctuations in oxygen consumption comparing HeLa (cancer) and CHO (non-cancer) cells and response to external NAD(P)+/NAD(P)H. Mol Cell Biochem. 2005 May;273(1-2):161-7. doi: 10.1007/s11010-005-0326-2. [PubMed:16013451 ]
Kim MY, Zhang T, Kraus WL: Poly(ADP-ribosyl)ation by PARP-1: 'PAR-laying' NAD+ into a nuclear signal. Genes Dev. 2005 Sep 1;19(17):1951-67. doi: 10.1101/gad.1331805. [PubMed:16140981 ]
Bruzzone S, Moreschi I, Guida L, Usai C, Zocchi E, De Flora A: Extracellular NAD+ regulates intracellular calcium levels and induces activation of human granulocytes. Biochem J. 2006 Feb 1;393(Pt 3):697-704. doi: 10.1042/BJ20051302. [PubMed:16225456 ]
Ying W: NAD+ and NADH in cellular functions and cell death. Front Biosci. 2006 Sep 1;11:3129-48. doi: 10.2741/2038. [PubMed:16720381 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for NAD (MMDBc0029513)

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3D PDB for #<Metabolite:0x00007fdb6410b200>

SMILES for #<Metabolite:0x00007fdb6410b200>

INCHI for #<Metabolite:0x00007fdb6410b200>

Structure for #<Metabolite:0x00007fdb6410b200>

3D Structure for #<Metabolite:0x00007fdb6410b200>